JPS6219557A - Aryl ethanol hydroxylamine, manufacture and use for promoting production - Google Patents

Abstract

Aryl ethanol-hydroxylamines of the formula <IMAGE> in which Ar represents aryl or heteroaryl, each of which can optionally be substituted, and R represents alkyl, aryl, aralkyl, heteroaryl, heteroaralkyl or cycloalkyl, each of which can optionally be substituted, or physiologically tolerated salts thereof, exhibit animal growth-promoting properties. Intermediates therefor of the formula <IMAGE> with the exception of phenyl and p-bromophenyl, are also new.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to arylethanolhydroxylamines, to processes for their preparation, and to their use as livestock production promoters.

Arylethanolamine is a known compound. Its pharmaceutical properties vary depending on its chemical structure. Among them, certain arylethanolamines are associated with weight gain in livestock;
and affects self-sealing fat ratio (EP-O5 (Eurotsu Publication Specification) No. 26.298). In this connection too, the basic structure of the arylethanolamine appears to be critical to this effect.

Formula I wherein both Ay represent optionally substituted aryl or heteroaryl, and each R represents optionally substituted alkyl, aryl, aralkyl, heteroaryl, heteroaralkyl or cycloalkyl arylethanolhydroxylamines and their physiologically acceptable salts, enantiomers and noastereomers have been found.

Formula ■ O0O Ay-C CM=Poison ■-R ■ In the formula, both Ar represent optionally substituted aryl or heteroaryl, and R represents optionally substituted alkyl, aryl, aralkyl, heteroaryl , heteroaralkyl, or cycloalkyl, wherein Ar and R have the above-mentioned meanings. Ta.

Formula ■ 0 0゜Ay-Ashi-CH=Kotoki■-R ■ In the formula, Ar is phenyl or U, both of which may be substituted.
Novel arylglyoxalnitrones have also been found in which R represents 7-aryl or heteroaryl excluding p-bromophenyl t- and R represents optionally substituted alkyl, aralkyl, heteroaralkyl or cycloalkyl.

2■! I A r -C-CHOm wherein lr represents aryl or heteroaryl, excluding phenyl and P-bromophenyl t-, both of which may be substituted, and the arylglyoxal with its hydrate or alcohol, as appropriate. In the form of an adduct of the formula ■H N-Ry, in which R represents an optionally substituted alkyl, aralkyl, heteroaralkyl, or cycloalkyl, the reaction is performed with hydroxylamine while removing water. A novel method for producing arylglyoxalnitrones has also been found, characterized by the formula: (E) Af-group 10H-Shu (E) (E) where Ar and R have the above meanings.

It can be used as a production promoter in the feed area. This property is surprising. This is because it is a well-known fact that changing the substitution of the amine moiety of the arylethanolamine molecule significantly changes its biological and pharmaceutical effects. Therefore, it was completely unexpected that a compound from a completely different chemical class, namely hydroxylamine, would exhibit economically viable effects.

Preferred arylethanolhydroxy-amines of formula I are those in which any Af is alkyl, halo-noalkyl, aryl, alkoxy, halogenoalkoxy, halodane, nitro, hydroxyl, cyano, alkoxyamino, alkylcarbonyl, amine, amino Carbonyl, dialkylaminocarbonyl, alkyl- and so-alkylamino, alkylaminocarbonyl, aminosulfonyl, alkylsulfonyl, alkylsulfinyl, alkylthio, halo-noalkylthio, alkoxycarbonylamino, aminocarbonylamino, alkylenedioxy, halo-noalkylenethio phenyl, naphthyl, optionally substituted with one or more identical or different substituents selected from the group consisting of oxy, cy, optionally substituted aryl, aryloxy and aryl; represents furyl, chenyl, zerimidinyl, pyrrolyl, thiazolyl, oxacylyl, pyrazolyl, imidazolyl, carbazolyl, fluorenyl, pyridazunyl, carbostistyryl, indolyl, pyrazinyl, quinolyl, isoquinolyl or zeridyl, and R is alkyl, alkenyl, .

alkoxy, alkylthio, hydroxyl, halogeno,
straight-chain or branched alkyl, cycloalkyl or bicyclo having up to 12 C atoms, optionally substituted by aryl, heteroaryl or aryloxy, which may be substituted; It is an alkyl.

Preferred as suitable substituents for groups which may be substituted are cyanide, halogens such as fluorine, chlorine or bromine, hydroxyl, C1-.

-alkoxy, C8-4-halogenoalkyl, phenyl, CIN4-alkoxy, C3,4-halogenoalkylcy, C1N4-alkylthio and C8-, -halogenoalkylthio. When a substituent is present on a phenyl group, in addition to the above, methylenedioxy, ethylenedioxy, halogeno-substituted methylenedioxy and halogeno-substituted ethylenedioxy, as well as one or more of the above-mentioned substituents Phenyl or phenoxy which may have radicals is preferred.

Particularly preferred compounds of formula I are those in which Ay is C1,4-alkyl, phenyl, C1,4-alkoxy, halogeno, especially fluorine, chlorine and bromine, cyanide, nitro-K.

CI, 4-halogenoalkyl, amino, C1-4-alkylamino, no (Ct~.

-alkyl)amino, C1~, -alkoxycarbonyl, aminocarbonyls (' I A,, 4-alkylaminocarbonyl, di(CI2.-alkyl)aminocarbonyl, aminosulfonyl, C%~4-alkylaminosulfonyl, di (Ct-4-alkyl)aminosulfonyl, C8,,,4-alkylsulfonyl, C1
~4-alkylsulfinyl, CI~4-alkylthio, C1-4-alkoxycarbonylamino, hydroxy, C1-4-halogenoalkyl, 01-4-halogenoalkylthio, methylenezoxy, ethylenedioxy, halo-rnometherenthoxy and phenyl substituted one or more times by the same or different groups selected from the group phenoxy, which may itself be substituted by one of the above-mentioned groups, and R represents 12 C3,4-alkynyl, C,N,-alkenyl, hydroxyl, halo, chlorine or bromine, and especially halogeno, C8,4-alkoxy, C8,4-alkyl and straight-chain or branched alkyl C which may be substituted by phenyl which may be substituted by nitro.

Furthermore, Ar in the formula is phenyl, C8,4-alkyl, 01-4-halogenoalkyl, cyan, hydroxyl, amine, C6-
represents phenyl substituted with 1, 2 or 3 same or different substituents selected from the group consisting of 4-alkyl and 4-alkylamino, halogen and nitro, and R is 8 and C8-4-alkynyls C2-4-alkenyl.

Hydroxyl, halogen, and especially methoxy, C8
Formulas representing straight-chain or branched alkyl or cycloalkyl optionally substituted by 4-alkyl, nitro, CF, and phenyl optionally substituted by halogens such as chlorine or fluorine Compound (2) is particularly suitable.

Ay in the formula represents phenyl substituted with one or more substituents selected from fluorine, chlorine, bromine, amine and CM, and R is C3-6-cycloalkyl, particularly cyclopropyl, ethynyl, Compounds representing C8-,-alkyl optionally substituted by hydroxyl, halogen or phenyl which may itself be substituted by fluorine or chlorine, trifluoromethyl or methoxy are especially Should be mentioned.

In addition to the compounds listed in the examples, mention may also be made of the following compounds No. 2.

Ar Rt The compounds of formula I can exist in the form of each of its enantiomers and also in the form of diastereomers if several optically active C atoms are present in the molecule.

Physiologically acceptable salts of compounds of formula (1) are formed with the following acids:

Hydrochloric acid, sulfuric acid, phosphoric acid, perchloric acid, hydrobromic acid, hydroiodic acid, hydrofluoric acid, nitric acid, acetic acid, oxalic acid, malonic acid, succinic acid, ascorbic acid, apple L, tartar L, maleic acid, Fumaric acid, methanesulfonic acid, benzoic acid, substituted benzoic acid, ic acid, chloroacetic acid, toluenesulfonic acid, benzenesulfonic acid, trichloroacetic acid, phthalic acid, naphthalenesulfonic acid and nicotinic acid.

Compounds of formula I are obtained by reduction of aryldarioxalnitrones of formula II. This reaction can be represented by the following equation.

Some arylglyoxalnitrones of the formula ■ are new substances (Blackgtal, D.) Austrian Chemical Journal (Aunt, /).

CAgm) (1978) 31 2013-22)
. Its manufacture is described below. Preferably used formula■
The arylglyoxalnitrones are such that the radicals 4r and R have the meanings indicated as preferred for the compounds of formula I.

This reaction is preferably carried out using the following reducing agents. Complex hydrides, such as alkali metal borohydrides such as N a B H4, N a B Hs CN.

LiBH, and N a B where the sum of X and y is 4
Hx (0-7le#/') 9'. Particularly preferred is NaBE.

This reaction is preferably carried out in the following diluent.

Inert organic solvent. This applies in particular to aliphatic and aromatic, sometimes halogen-substituted hydrocarbons, such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, ligroin, benzene, toluene, methylene chloride, ethylene chloride, chloroform, Carbon tetrachloride, chlorobenzene and O-sochlorobenzene, as well as ethers such as soether ether, dibutyl ether, diglycol methyl ether, tetrahydrofuran and duoxane; In addition, esters such as methyl and ethyl acetate; and nitriles such as acetonitrile and pro2onitrile, benzonitrile and glutarosonitrile; and also amides such as dimethylformamide, dimethylacetamide and N-methyl Includes pyrrolidone: as well as trimethyl sulfoxide, tetramethylene sulfone and hexamethylene phosphate triamide.

This reaction is carried out at a temperature of -50 to 100°C, preferably 0°C.
It is carried out at a temperature of 50°C to 50°C.

Work-up is carried out using conventional techniques.

Arylglyoxalnitrone of formula (■) is a new substance. These are obtained by reacting the arylglyoxal of formula (2) with the N-alkylhydroxylamine of formula (1). This reaction is then expressed as tK.

Some of the arylglyoxals mentioned in 2) are known substances. The novel arylglyoxals can be prepared by methods known per se, for example by oxidizing the corresponding α-halo-noacetophenones with DMSO or by oxidizing acetophenones with selenium dioxide. .

Preferably used arylglyoxal in formula (2) is one in which Ar has the meaning indicated as preferred for the compound of formula (2).

The following aryl oxals may be mentioned in particular:

Hydroxylamine of formula (2) is a known substance, or it can be produced by a known method.

The preferably used hydroxylamine of formula (2) is R in the formula
has the meaning as indicated as preferred for the compounds of formula I.

This reaction can be carried out in a diluent or without a diluent. The following may be mentioned as diluents.

All inert organic solvents. This includes in particular aliphatic and aromatic hydrocarbons, which may be halodane-substituted, such as pentane, hexane, hegetane, cyclohexane, petroleum ether, benzine, ligroin, benzene, toluene, methylene chloride, ethylene chloride, chloroform,
Carbon tetrachloride, chlorobenzene and O-dichlorobenzene; alcohols such as methanol, ethanol, isopro9ol, glycols and longer chain alcohols; and ethers such as trimethyl ether,! Ethyl ether, glycol dimethyl ether and sogelicolutz methyl ether, tetrahydrofuran, and duoxane; in addition, ketones such as acetone, methyl ethyl ketone, methyl in butyl ketone and methyl in butyl ketone; also esters,
For example, methyl acetate and ethyl acetate; and nitriles, such as acetonitrile and propionitrile, benzonitrile and geltalodinitrile, as well as
Amides such as dimethylformamide, trimethylacetamide and N-methylpyrrolidone; and trimethylsulfoxide, tetramethylene sulfone and hexamethylphosphoric triamide.

An N-alkylhydroxylamine of the general formula (2) as a salt of an inorganic or organic acid with an arylglyoxal of the general formula (2) and an alkali metal salt of a weak organic acid, such as acetic acid.
It is preferable to carry out the reaction in the presence of IJum.

This reaction is carried out at 10-200°C, preferably 50-150°C.
It can be carried out at a temperature of, very particularly preferably at the boiling point of the solvent.

This reaction is preferably carried out in the presence of a water removing agent. Examples include Nα, SO, , Mg5O, %K
COCaCL, MoVki: L! S%
Grow-sheep, silica glue and aluminum hydroxide. Water formed during the reaction can also be removed azeotropically from the reaction mixture.

Compounds (2) and (2) are preferably used in equimolar ratios.

Post-processing is carried out using methods known per se.

General formula in any case! It is not necessary to isolate the arylglyoxalnitrone of general formula (2) in order to prepare the N-hydroxyarylethanolamine of formula (2). It has been proven that it is advantageous to carry out this reaction continuously as a one-tank reaction.

The active compounds are useful as production promoters in livestock for promoting and accelerating growth, milk and hair production, and for feed efficiency,
Used for improving meat quality and shifting the meat/fat ratio towards a meat predominance. The active compounds are useful for breeding, ornamental and pet livestock.

Useful and breeding livestock include mammals such as cattle, pigs, horses, sheep, goats, domestic rabbits, hares, spotted deer, fur animals such as mink and chinchillas; birds;
Examples include chickens, geese, ducks, turkeys and pigeons; fish, such as carp, trout, salmon, rabbits, tench and rockfish; and reptiles, such as snakes and crocodiles.

Ornamental and pet domestic animals include mammals such as dogs and cats, birds such as hawks and canaries, and fish such as ornamental and aquarium river fish such as goldfish.

The active compounds are used at all stages of livestock growth and production, irrespective of the sex of the livestock.

The active compounds are preferably used during the active growth and production stages. ; depending on l-fi, the phase of vigorous growth and production lasts from 1 month to 10 years.

The amount of the active compound administered to livestock to achieve the desired effect depends on the favorable properties of the active compound.
It can be varied within a wide range.

Preferably the daily dose is about 1 to 50 η C9 (LOOl to 50η, in particular α01 to 5 capes per day). A reasonable amount of active compound and a reasonable duration of administration will depend, in particular, on the species, age, and age of the livestock. , sex, phase of growth and production, health status and nature of the housing and feed, but can be easily determined by any person skilled in the art.

The active compounds are administered to livestock in a conventional manner.

The mode of feeding varies depending on, among other things, the livestock's diet, behavior, and health status.

Although the active compounds may be administered at once, the compounds may be administered at any time or throughout the growth and production stages.
Alternatively, it is also possible to administer continuously through a portion thereof.

Continuous administration may be administered once or several times a day, and at regular or irregular intervals.

Administration may be carried out orally or parenterally,
They may be administered in pure form as well as in combinations suitable for this purpose.

The active compounds may be present alone or in combination with other production-promoting actives, mineral feeds, trace element compounds, vitamins, non-tank compounds, colorants,
Antioxidants, flavoring agents, flow modifiers, preservatives and pelleting aids may also be present in admixture.

Other production-promoting active compounds are, for example, tylosin (
tyLozi+%) Ohyohihajiniamaishi7 (vi
There are antibiotics such as ryirliamyzin. Examples of mineral feeds are dicalcium phosphate, magnecrum oxide and sodium chloride. Examples of trace element compounds are iron fumarate, sodium iodide, cobalt chloride/copper tosulfate and zinc oxide. Examples of vitamins are vitamin A, vitamin D8, vitamin E, vitamin B and vitamin C. Examples of non-toxic compounds are biuret and urea. Examples of colorants are carotenoids such as citranaxanthene, zeaxanthin and cabanthin. Examples of antioxidants are ethoxyquin and butylated hydroxytoluene. An example of a fl agent is vanillin. Examples of emulsifiers are lactic acid esters and lecithin. Examples of flow modifiers are sodium stearate and calcium stearate. Examples of preservatives are citric acid and propionic acid. Examples of pelletizing aids are lignin sulfonates and cellulose ethers.

The active compounds may be administered with feed and/or drinking water.

Feed includes immiscible feeds of plant origin, such as hay, root crops and grain by-products; immiscible feeds of animal origin, such as meat, fats, dairy products, bone meal and fish products; immiscible feeds, such as vitamins, tannery, and amino acids. Examples include DL-methionine; and salts such as lime and sodium chloride. Feed further includes mixed feed and mixed feed. This includes unmixed feeds with a composition that ensures balanced nutrition with respect to the supply of energy and tongue, as well as with regard to the supply of vitamins, mineral salts and trace elements.

The active compound concentration in the feed is usually about Q,01~soop
pm, preferably 0.1-50PP77! It is.

The active compounds may be added to the feed alone or in the form of premixes or feed concentrates.

Examples of poultry feed compositions containing the active compounds according to the invention: Wheat 200L) Corn 540g, Soybean flour 3611
, 60 g of beef tallow, 15 S of dicalcium phosphate, 101 of calcium carbonate, 4 fI of iodized sodium chloride, 7.5.9 of the vitamin/mineral mixture and 2.5 I of the active compound premix are carefully mixed to form the feed for IkII.

1kl? The feed mixture contains the following substances:

Vitamin A6QQ1. U, , Vitamin D, 1001,
U, , Vitamin E10”llF, Vitamin 31ry
is riboflavin 31q, pyridoxine 211i, vitamin B1,2Qmc g, a#calcium ntthenate 5■, ==rtinic acid 50'lf, choline hydrochloride 20 Q+
lv, MnS 04.11.0 200I%Zn5O
,・7H,014017JP,FgS04・7H,01
00'li and Cμso4・5 Ht 020'9
2.5 g of active compound premix is, for example, active compound 1Qq, DL, -methithinine II! , and the remaining amount of soybean flour.

Examples of feed compositions for pigs containing the active compounds according to the invention: 6 sol/feed grain flour (consisting of 200 g of corn, 150 g of barley flour, 150 g of oat flour and 150 I wheat flour), 80 g of fish meal, 60 g of soybean flour, Cassava flour 60fi, brewer's yeast 58y, vitamins for pigs/
Mineral mixture 50.9, castor bean meal powder, corn gluten feed, soybean oil 10g, sugarcane molasses 10. ! i
+ and active compound premix (composition is e.g. chicken)
1)C9 by carefully mixing 2g (same as IJ feed)
used as feed.

Although these feed mixtures are preferably designed for feeding and fattening of chickens and pigs, they may also be used in the feed of other livestock with the same or similar composition.

Example A Rat breeding trial SPF WiztcLr type (/1-f-y
Female laboratory rats (bred by Haggmtt Lulu) weighing 90-110 g were randomly assigned to
They were fed standard rat chow supplemented with the desired amount of active compound. Each trial was designed to use the same batch of feed so that differences in feed composition would not compromise the comparability of the results.

Rats were given water at random.

Each trial group consisted of 12 rats, which were fed a diet supplemented with the desired amount of active compound. The control group received a diet containing no active compound. To ensure comparability between trial groups, the average body weight and body weight differences of rats in each trial group were kept the same.

Weight gain and feed consumption were measured during the 15 day trial.

The results obtained are shown in the table.

Table 1 Examples Example 1 N-t-butyl-N-2-hydroxy-2-phenylethylhydroxylamine C'6H, -CHoH-CH, -N-C (CH8).

Product N-t-1 tylphenylglyoxalnitrone 5y 1
N a BE dissolved in 50 d of methanol,
1.81 was added in portions at room temperature. After 3.4 hours, the mixture is evaporated in a rotary evaporator, the residue is cooled, 100% strength HCl is added, the mixture is extracted three times with 25 portions of ether, and the aqueous phase is cooled. At the same time, 120% of a 10% strength aqueous sodium hydroxide solution was added to make it alkaline. The aqueous phase was extracted several times with dichloromethane and the organic phase was dried over sodium sulphate and evaporated.

The residue was dissolved in 50 mL of ether and 150 d of a saturated ether solution of oxalic acid was added. The oxalate precipitate thus obtained was isolated and recrystallized.

Yield: 2.71 Melting point: 143-144°C The compound of formula (1) in the table below can be obtained in the same manner.

a-OH,y,-CH5OCO-C,H,--C(CM
s).

5.5-CL,,4-CH,QCclH,--C(CH
,)35-Cl, a-NO, C6H, --C(CH8
).

5.5(?Zt, 4-ME, -C6H, -C(C1,
), (Fumarate] 4 cg, co%5-'CM, S
-C,H,--C(CH,).

4 0H%3-HOCH, -C,H,, -C(CH,)
.

a-OH,5-CH,So,NH-C,H,-i-globil2.5 (CHsOLCsHs
t-Butyl (value of F: on DC silica F254, 0.2 plots, fluid phase: toluene:ethanol = 3-:1 = 0.365) Production example of oily starting material α1 N-1,5,5 -trimethylglobylphenylglyoxaladonitron CO C,H,CO-CM=N■-cH (cps > -c
(cps) s5.5-Thmethyl-2-butylhydroxylamine hydrochloride 5g, sodium acetate 2.6g and phenylglyoxal hydrate 5.711-100dO were placed in ethanol and stirred at room temperature for 2.5 hours. This mixture was passed through, and the F solution was evaporated to a concentration of 10-, and 20- of water was added thereto. After cooling to 1° C. for 1 hour, the resulting precipitate was separated by F and recrystallized from methanol/water.

Yield: 5g Melting point: 134-135℃ Formula ■ in the table below
The compound was also produced in the same manner.

α20 4-NH,,5,5-CL, -C6H.

α214-ME, 5, 5-CLt C6H! α2
2 4-NH,,5,5C't'act(123
4-NH, %5, 5-CZ, -C6H.

-CH', -CH(CH,)t
Oily -CH(CH,)CH,-4-F-C6H4
Oily -CH(CH,) -CM, -2-CZ, 6-
F-C8H, oily -CH, -CH, -5,4-0M30
-C,H4 Oil Example 6 The fine hydroxylamines shown in the table below are prepared by known methods.

Method α) = Emmonz (F, D, Emmonz), Journal of the American Chemical Society (/, Am, ('Ags.

Sac,) 79.5739-54, (1957) Method b) = Porch (R, BOrCh), Journal of the American Chemical Society (/, Am, Chgm, Sac,) 95.289
7, (1971) h 1 2 Clb 16
C(C,H,), -CH-NHOHb 17
C(H,), CH-CH(CH3)-Nh1
8 CH8(CM, 0H)-CHNHOHhl
9 (rLCs 11?) (?H
s CHN H0Eh) b) b) h) b) VOHh ) b) h) h 21 (C, II,), -CIINH
OHh)

Claims (1)

[Claims] 1. Formula I ▲ Numerical formulas, chemical formulas, tables, etc. are included ▼ In the formula I, both Ar represent an optionally substituted aryl or heteroaryl, and both R are optionally substituted. Arylethanolhydroxylamines representing alkyl, aryl, aralkyl, heteroaryl, heteroaralkyl or cycloalkyl and their physiologically acceptable salts, enantiomers and diastereomers. 2. Formula II ▲ Numerical formulas, chemical formulas, tables, etc. ▼ II In the formula, both Ar represent optionally substituted aryl or heteroaryl, and R represents optionally substituted alkyl, aryl, aralkyl, Formula I characterized by the reduction of arylglyoxalnitroso representing heteroaryl, heteroaralkyl, or cycloalkyl I ▲There are mathematical formulas, chemical formulas, tables, etc.▼ I In the formula Ar and R have the above meanings A method for producing arylethanol hydroxylamine. 3. Formula II ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ II In the formula, Ar represents aryl or heteroaryl excluding phenyl and p-bromophenyl, both of which may be substituted, and R is both substituted. Arylglyoxalnitrones may also represent alkyl, aralkyl, heteroaralkyl or cycloalkyl. 4. Formula III ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ III In the formula, Ar represents aryl or heteroaryl, excluding phenyl and p-bromophenyl, both of which may be substituted, as appropriate. In the form of its hydrate or adduct with alcohol, formula IV ▲ mathematical formula, chemical formula,
There are tables, etc. ▼ IV Formula II, which is characterized by reacting with hydroxylamine in which R represents optionally substituted alkyl, aralkyl, heteroaralkyl, or cycloalkyl while removing water ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ II A novel method for producing arylglyoxalnitrone in which Ar and R have the above meanings. 5. A livestock production promoter characterized by containing the arylethanolhydroxylamine of formula I according to claim 1. 6. Animal feed, livestock drinking water, and additives for animal feed and livestock drinking water, characterized by containing the arylethanol hydroxylamine of formula I according to claim 1. 7. Use of the arylethanol hydroxylamine of formula I according to claim 1 for promoting livestock production. 8. A method for producing a livestock production promoter, which comprises mixing the arylethanol hydroxylamine of formula I according to claim 1 with a filler and/or diluent. 9. Animal feed, characterized in that the arylethanol hydroxylamine of formula I according to claim 1 is mixed with feed or drinking water and optionally other auxiliaries;
A method for producing an additive for livestock drinking water or animal feed and for livestock drinking water. 10, N-2-(4-amino-3,5-dichlorophenyl)-2-hydroxyethyl-Nt-butylhydroxylamine.